And we have the leadership to help you get there.

The Consulting

Director, Strategy & Transformation serves as a strategic partner to CNA Canada's executive leadership team, responsible for translating business strategy into executable plans and measurable outcomes. This role leads enterprise strategy execution, transformation initiatives, governance, and change management activities that enable business growth and operational effectiveness. Working across business units and enabling functions, the Director drives alignment, prioritization, accountability, and business readiness to ensure strategic initiatives deliver intended value.

Success in this role requires strong business acumen, executive influence, program leadership, and the ability to mobilize stakeholders around shared priorities while fostering a culture of execution, innovation, continuous improvement, and accountability. Lead the development, execution, and ongoing management of CNA Canada's strategic business plan, ensuring alignment between business objectives, initiatives, investments, resources, and measurable outcomes. Facilitate annual planning, prioritization, and roadmap development activities to translate strategic priorities into executable plans and delivery commitments.

Partner with executive leadership to identify strategic opportunities, optimize operating models, and advance enterprise transformation priorities. Lead cross-functional strategic and transformation initiatives, ensuring delivery against objectives, timelines, budgets, and expected business outcomes. Establish governance, reporting, and performance management practices that support effective decision making, accountability, and enterprise alignment.

Monitor strategic initiatives, identify risks, dependencies, and barriers to execution, and recommend actions to maintain momentum and achieve results. Drive business readiness, organizational change management, and stakeholder engagement activities to support successful implementation and adoption of strategic initiatives. Facilitate collaboration across business units and enabling functions to improve organizational effectiveness, streamline processes, and maximize performance.

Conduct industry research, competitive analysis,



and benchmarking to inform strategic recommendations and business decisions. Develop executive-level presentations, assessments, business cases, and recommendations to support leadership discussions and decision making. Define and monitor key performance indicators, reporting, and dashboard capabilities to measure strategic progress, business impact, and benefits realization.

Identify opportunities to leverage data, analytics, automation, artificial intelligence, and digital capabilities to enhance business performance and accelerate Reporting Relationship Typically AVP or above Demonstrated ability to lead enterprise-wide strategic and transformation initiatives involving multiple stakeholders and significant organizational change. Strong executive presence and influencing skills with the ability to build alignment, challenge thinking, and effectively partner with senior leadership teams. Strong business and financial acumen, including experience evaluating investments, prioritizing initiatives, and measuring business value.

Excellent communication, facilitation, stakeholder management, and executive presentation skills.

Experience leading program management, governance, and organizational change initiatives. Highly adaptable, results-oriented, and accountable, with the ability to manage multiple priorities in a dynamic environment. Strong knowledge of Microsoft Office Suite and other enterprise business tools, including responsible use of AI-enabled technologies (such as Copilot or similar) to enhance efficiency, analysis and workflow in accordance with company policies.

Education & Experience Bachelor's degree required; Master's degree or relevant professional designation preferred. Minimum 8 years of progressive experience in strategy, consulting, transformation, program management, or related business leadership roles.





Commercial

Lines experience considered an asset. Demonstrated experience partnering with executive leadership teams to drive strategic planning, organizational change, and enterprise transformation initiatives. Our total rewards philosophy reflects our commitment to building a high-performing, inclusive culture where every team member is empowered to grow, contribute, and thrive.

We value the unique strengths and perspectives each individual brings to our business, our clients, and our communities. The base salary range for this position is $135,000 - $170,000, complemented by a comprehensive and competitive benefits package to help our employees - and their family members - achieve their personal, financial, emotional, and social wellbeing goals. Base salary determinations are based on various factors, including but not limited to, relevant work experience, skills, certifications and location.

It is our policy to provide equal employment opportunities to employees and applicants based on job-related qualifications and ability to perform a job. If a selected applicant requests accommodation during the recruitment process, CNA will consult with the applicant in order to provide suitable accommodation that takes into account the applicant’s accessibility needs. We strive to connect people, departments and business areas, to function as a team, and to serve our customers and communities with professionalism and respect.

Our dedication to employee engagement, continuous learning and the open exchange of ideas is the cornerstone of our business. These ideals, combined with our focus on the customer, enable us to explore current market opportunities and build on our success. At CNA, we are committed to advancing a culture of inclusion - one that attracts talent from all walks of life, foster respect and collaboration, and enables all of our colleagues to do their best work.

At CNA, we have a long standing commitment to the diverse communities in which we live and work.

Corporate Social

Responsibility is not one person, or one department, it's the entire enterprise coming together to make the world a better place. #

📌 Consulting Director, Business Strategy & Transformation (Toronto)
🏢 01705 Continental Casualty Company-canada
📍 Toronto